This invention relates to novel organosilicon compounds and processes for preparing the same. More particularly, it relates to novel organosilicon compounds having an organooxysilyl group at one end of a molecule and a monovalent hydrocarbon group at the other end thereof and containing a polysulfide group as well as novel organosilicon compounds having organooxysilyl groups at both ends of a molecule and containing a divalent hydrocarbon group flanked with polysulfide groups at a center thereof.
Compounds containing alkoxysilyl and polysulfide groups within the molecule are known in the art. These compounds are used as an interfacial binder between inorganic materials such as silica, aluminum hydroxide and talc and organic materials such as thermosetting resins, thermoplastic resins and rubber, an adhesion modifier for organic resins and rubber, a primer composition or the like.
While sulfide group-containing organosilicon compounds are applied to composite materials composed of resins or rubber and inorganic materials as mentioned above, compositions obtained by adding known sulfide group-containing organosilicon compounds to resins or rubber and mixing them with inorganic materials suffer from insufficient abrasion resistance.
An object of the invention is to provide novel organosilicon compounds having overcome these disadvantages and drawbacks, and processes for preparing the same.
In one aspect, the invention provides an organosilicon compound having the following general formula (1):
xe2x80x83(R1O)(3-p)(R2)pSixe2x80x94R3xe2x80x94Smxe2x80x94R4xe2x80x94Axe2x80x83xe2x80x83(1)
wherein R1 and R2 each are a monovalent hydrocarbon group having 1 to 4 carbon atoms, R3 and R4 each are a divalent hydrocarbon group having 1 to 10 carbon atoms, A is hydrogen or the moiety: xe2x80x94Smxe2x80x94R3xe2x80x94Si(OR1)(3-p)(R2)p, m is 2 to 10, and p is equal to 0, 1 or 2.
In one embodiment of the process according to the invention, the organosilicon compound of formula (1) is prepared by the step of reacting a haloalkyl group-containing organosilicon compound of the following general formula (2):
(R1O)(3-p)(R2)pSixe2x80x94R3xe2x80x94Xxe2x80x83xe2x80x83(2)
wherein R1 and R2 each are a monovalent hydrocarbon group having 1 to 4 carbon atoms, R3 is a divalent hydrocarbon group having 1 to 10 carbon atoms, X is halogen, and p is equal to 0, 1 or 2, and a halogen-containing compound of the following general formula (3):
Xxe2x80x94R4xe2x80x94Yxe2x80x83xe2x80x83(3)
wherein R4 is a divalent hydrocarbon group having 1 to 10 carbon atoms, X is halogen, and Y is hydrogen or halogen, with an anhydrous sodium sulfide or polysulfide having the following general formula (4):
Na2Sqxe2x80x83xe2x80x83(4)
wherein q is 1 to 4, and optionally, sulfur.
In another embodiment of the process according to the invention, the organosilicon compound of formula (1) is prepared by the step of reacting a mercaptoalkyl group-containing organosilicon compound of the following general formula (5):
(R1O)(3-p)(R2)pSixe2x80x94R3xe2x80x94SHxe2x80x83xe2x80x83(5)
wherein R1 and R2 each are a monovalent hydrocarbon group having 1 to 4 carbon atoms, R3 is a divalent hydrocarbon group having 1 to 10 carbon atoms, and p is equal to 0, 1 or 2, with a sulfenamide group-containing compound of the following general formula (6):
(R5)(R6)Nxe2x80x94Sxe2x80x94R4xe2x80x94Bxe2x80x83xe2x80x83(6)
wherein R4 is a divalent hydrocarbon group having 1 to 10 carbon atoms, R5 and R6 each are independently hydrogen or a monovalent hydrocarbon group having 1 to 6 carbon atoms, with the proviso that R5 and R6 are not hydrogen at the same time, or R5 and R6, taken together, form a divalent hydrocarbon group having 4 to 10 carbon atoms which may contain a nitrogen, oxygen or sulfur atom, and B is hydrogen or the moiety: xe2x80x94Sxe2x80x94N(R5)(R6).
In a further embodiment of the process according to the invention, the organosilicon compound of formula (1) is prepared by the step of reacting a sulfenamide group-containing organosilicon compound of the following general formula (7):
(R1O)(3-p)(R2)pSixe2x80x94R3xe2x80x94Sxe2x80x94N(R5)(R6)xe2x80x83xe2x80x83(7)
wherein R1 and R2 each are a monovalent hydrocarbon group having 1 to 4 carbon atoms, R3 is a divalent hydrocarbon group having 1 to 10 carbon atoms, R5 and R6 each are independently hydrogen or a monovalent hydrocarbon group having 1 to 6 carbon atoms, with the proviso that R5 and R6 are not hydrogen at the same time, or R5 and R6, taken together, form a divalent hydrocarbon group having 4 to 10 carbon atoms which may contain a nitrogen, oxygen or sulfur atom, and p is equal to 0, 1 or 2, with a mercapto group-containing compound of the following general formula (8):
HSxe2x80x94R4xe2x80x94Zxe2x80x83xe2x80x83(8)
wherein R4 is a divalent hydrocarbon group having 1 to 10 carbon atoms, and Z is hydrogen or SH.